How to Quit Your Job (successfully) and Be Happy (forever)

Ultimately, this is not a tale of money, power, or “sticking it to the man”, but examples of working towards happiness and fulfillment with your career. In this post I want to give you tips about how to quit your job successfully* to pursue something that gives meaningful value to your time.

It is possible to work a job that you don’t love (all the way) and still be happy. There are other ways to pursue passions, projects, and hobbies without making them your career – in fact, I think a lot of passions are best left as that.

I want to put a disclaimer on this advice, because my facts and circumstances will likely differ from yours. No matter where you’re starting from, however, these teachings will be applicable. Some of my advantages include the fact that I am white, male, have no debt from college, and my parents were very encouraging. This support system alone provided me an inherent level of stability.

That being said, I took none of it for granted. I worked, hard, to earn everything I have achieved thus far. I don’t complain a lot, I put my head down to grind, and I am relentless in my pursuit of growth. That’s something your parents can’t teach you – it’s a decision you have to make every morning and every night. You must flex and develop this “growth” muscle on your own, through blood, sweat, and tears.

Assuming you have found something you might like to pursue, the below will serve to help guide your thinking and framework.

#1 – Who is already doing it?Your preliminary search into a new field likely returned several answers to this question. If you want to be a yoga teacher, look into studios in your area. If you want to be an investment banker, chances are someone from your high school or college is working in the field, especially in a bigger city. Seek out similar stories to yours – chances are everyone working your dream job didn’t start there.

#2 – Find a mentorThis might be the most important point in here. Every great practitioner loves to teach his or her craft, especially to someone young, humble, and hungry to learn. This window can help you decide if the ups and downs of this new career are really for you. Mentors have practical experience over a long period of time, have a network of relationships to assist you, and can give you a one-on-one learning environment. This alone is invaluable.

Their career path can be a road map to emulate success, however, it is to be put into the context of today’s environment. The way we communicate, work, learn, and connect is different, as is the workplace. Apply what you have already learned to this new mentor knowledge, and make the best choices available.

#3 – Seek peer relationshipsAlmost just as important as the mentor relationship, your peer relationships give you insight into the entry-level position of your new career. If your mentor is a VP, it is unlikely their day-to-day life will be anything like yours. It’s great to know what your career might turn out like, but it’s also helpful to know what it will be like right away.

#4 – Speak with as many people as possible in relatable fieldsLive Better essentially started this way. We spoke with countless people on the phone and via email asking only one question – “We are starting a business (at the time making superfood protein bars) and really love the work you do. If we can jump on the phone for 20-30 minutes, we’d love to talk about your successes and get some advice on how to go about (insert topic) to grow our business.”

This line of questioning also works wonders when asking for help in finding a job in your desired field. People often feel like they are burdening others with a request such as this, however, you have something to offer them as well. Networks grow when more branches are formed. Even if you are not able to help immediately, or if they are unable to help you immediately, that doesn’t mean that just a few weeks later your name won’t be top of mind when someone comes asking for a good candidate for whatever job opening. Lessen your degree of separation from everyone.

Just smile and wave, people.

#5 – Overlap your old job and your new jobWhen preparing to start my personal training business as well as Live Better, I was simultaneously a tax consultant at a Big 4 accounting firm. From personal trainer, Nike trainer, superfood protein bar maker, podcaster, and yoga teacher to senior associate in tax, all at once. The best way to find out if you’ll love doing something long term is to start doing it, right now. Yes, the hours are going to suck. I woke up three hours before “work” started to train clients, went to the office for a few hours, ducked out to teach a Nike class for lunch, went back to the office for upwards of 8, 9 10 hours, came home to workout, then met with Bret (my business partner) to chat about whatever project we had going and finish my Live Better tasks for that day, often until well past 1am. And repeated that for months on end.

I had the dichotomy of tax consultant vs. health coach to remind me at the end of each day which I would rather be doing. Finally it became too much to handle both, and I made my decision. For me, it was easy at that point with months of experience encouraging me in one direction.

#6 – Make a budget and project your incomeOne of the hardest parts of making the jump is feeling secure. The main source of insecurity is largely financial for most people. It’s hard to give up a comfortable living (with great future earnings potential) to pursue your own, uncertain future. I’m here to tell you there is no price tag on mental freedom, working towards something you care about, and waking up with a pep in your step.

If the first thing you get out of bed for in the morning is something you have to do, and not something you want to do, your day is already off.

I had a very clear picture before I quit about what my earnings potential was in accounting. I also tried to project what I felt my time was worth, including what rate I would charge for new training services. I figured out how many hours I needed to train per week to earn more than my tax position, and calculated whether I would feel happy working that much.

I had enough clients to help me feel secure enough to pay rent, buy groceries, and generally do things for fun I loved, like travel. There was still enough to save a little bit, which was awesome right from the start.

Make a plan, budget, forecast, and stick to it. Exceeding these goals is the fun part!

#7 – Envision what success looks and feels likeAsk yourself, “What will it take to make me happy?” For some, this is a financial figure. “I want to make $100,000 per year.” For others, it might be “I want to work five hours a day, be able to travel where and when I want, and be home with my family every single night for dinner.”

This is an ever-moving target, and one that is hard to define. Mine sounded something like, “Earn enough money to save a little, spend a little, help someone every day have the best day ever through changing their fitness or lifestyle, and travel when the opportunity presents itself.”

I struggle with turning off my uber competitive nature to earn as much money as possible, to “win” at all costs, against feeling content with the fact that I am making a tangible change in several peoples’ lives every day doing exactly what I want to be doing. Ultimately, I hope both of these paths jive. I believe when you are passionately working to help others in the pursuit of something you love, the money will come.

#8 - Imagine the worst-case scenario…. is it really that bad?If you had the option, would your old job take you back? Could you remain financially stable for at least one to two months without your current income? Is moving back in with your parents the worst possible scenario?

Of course, death isn’t preferable. Not what I mean here. Envision what happens if you fail at your venture. Could you put that on a MBA application and go to business school to restart? Could you reapply to another firm that does similar work as your last job in pursuit of starting your own business?

I can promise you that putting something like “I tried to develop the next [Facebook], got [X number of] users to sign up, but ultimately failed at implementation for [X] reasons” is going to stand out against whatever the generic print is for applying to your next position.

Be interesting, and interesting conversations will follow.

#9 – Take note of things you’ve learned and people you respectIs someone you work with a really great leader? Why? What process or excel technique might be useful going forward? No matter how much you seemingly dislike your current job, there are translatable skills you can take with you. If there is one thing I took from my time in professional services, it’s that of conducting yourself like a business professional. This includes, but is not limited to, sending emails, setting meetings, giving speeches, shaking hands, handling (sometimes difficult) clients, concise writing techniques, and traveling.

Pay attention to what works, who does well, and how to perform as part of a team. This is invaluable, and will stay with you forever.

#10 – Value your relationships above all elseI made so many wonderful friends at my first job. When you work long hours, eat together, complain together, laugh together, and repeat, it’s easy to build some camaraderie. I got super lucky to have made “real” friends (as in hanging outside of work functions was fun) and will cherish those friendships forever. This included several people above my level.

Your friends are your first level of support. They become the cheers you hear from the crowd as you start out. Your network is the most valuable thing you own, and it should be protected at all costs.

#11 – Establish a “Board of Directors” for making decisionsSpeaking of relationships, you will need someone to bounce ideas off. I’d suggest a whole group of people. The same way a company establishes a board of directors, you should as well. This group can include your mentor, your parents, close friends whose opinion you respect, and someone who will keep your moonshot ideas on the right track.

This group backboard extends beyond your professional decisions. They can be utilized to make personal ones as well, especially your family and friends.

#12 – Make a leap of faithThe time will never be right. The stars won’t align. You (very likely) won’t win the lottery.

It’s time to make your own luck. You will be okay, you will be successful if you want it bad enough, and the time is right now. The little devil on your shoulder is going to try and convince you forever that a life of comfortable boredom and easy security is better than pushing your chips all in.